Erratum: Identification, synthesis, and biological evaluation of 6-[(6R)-2-(4-fluorophenyl)-6-(hydroxymethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a] pyrimidin-3-yl]-2-(2-methylphenyl)pyridazin-3(2H)-one (AS1940477), a potent p38 MAP kinase inhibitor (Journal of Medicinal Chemistry (2012) 55:17 (7772-7785) DOI: 10.1021/jm3008008);Identification, synthesis, and biological evaluation of 6-[(6 R)-2-(4-fluorophenyl)-6-(hydroxymethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a ]pyrimidin-3-yl]-2-(2-methylphenyl)pyridazin-3(2 H)-one (AS1940477), a potent p38 MAP kinase inhibitor

Journal of Medicinal Chemistry

Volumn 55, Issue 17, 2012, Pages 7772-7785

  Asano, Toru ^a   Yamazaki, Hitoshi ^a   Kasahara, Chiyoshi ^a   Kubota, Hirokazu ^a   Kontani, Toru ^a   Harayama, Yu ^a   Ohno, Kazuki ^a   Mizuhara, Hidekazu ^a   Yokomoto, Masaharu ^b   Misumi, Keiji ^b   Kinoshita, Tomohiko ^b   Ohta, Mitsuaki ^a   Takeuchi , Makoto ^a  

^a ASTELLAS PHARMA INC   (Japan)

^b WAKUNAGA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 [2 (4 FLUOROPHENYL) 4,5,6,7 TETRAHYDROPYRAZOLO[1,5 A] PYRIMIDIN 3 YL] 2 (2 METHYLPHENYL)PYRIDAZIN 3(2H)ONE; 6 [2 (4 FLUOROPHENYL) 5 (HYDROXYMETHYL) 4,5,6,7 TETRAHYDROPYRAZOLO[1,5 A]PYRIMIDIN 3 YL] 2 (2 METHYLPHENYL)PYRIDAZIN 3(2H) ONE; 6 [2 (4 FLUOROPHENYL) 6 (HYDROXYMETHYL) 4,5,6,7 TETRAHYDROPYRAZOLO[1,5 A]PYRIMIDIN 3 YL] 2 (2 METHYLPHENYL)PYRIDAZIN 3(2H) ONE; 6 [2 (4 FLUOROPHENYL) 6 HYDROXY 4,5,6,7 TETRAHYDROPYRAZOLO[1,5 A]PYRIMIDIN 3 YL] 2 (2 METHYLPHENYL)PYRIDAZIN 3(2H) ONE; 6 [2 (4 FLUOROPHENYL) 6 [(4 METHYLPIPERAZIN 1YL)METHYL] 4,5,6,7 TETRAHYDROPYRAZOLO[1,5 A]PYRIMIDIN 3 YL] 2 (2 METHYLPHENYL]PYRIDAZIN 3(2H) ONE; 6 [3 (4 FLUOROPHENYL) 5 [(3 HYDROXYPROPYL)AMINO] 1H PYRAZOL 4 YL] 2 (2 METHYLPHENYL)PYRIDAZIN 3(2H) ONE; 6 [6 (4 FLUOROPHENYL) 2,3 DIHYDRO 1H IMIDAZO[1,2 B] PYRAZOL 7 YL] 2 (2 METHYLPHENYL)PYRIDAZIN 3(2H) ONE; 6 [6 (4 FLUOROPHENYL) 6,7 DIHYDRO 5H PYRAZOLO[5,1 B][1,3]OXAZIN 3 YL] 2 (2 METHYLPHENYL)PYRIDAZIN 3(2H) ONE; AS 1940477; MITOGEN ACTIVATED PROTEIN KINASE P38; MITOGEN ACTIVATED PROTEIN KINASE P38 INHIBITOR; PYRAZOLE DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; TUMOR NECROSIS FACTOR ALPHA INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTHRITIS; ARTICLE; CELL ACTIVITY; CYCLIZATION; CYTOKINE PRODUCTION; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG HALF LIFE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; IN VITRO STUDY; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

EID: 84866306939     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501222p     Document Type: Erratum

References (33)

1. Grewal, I. S. Overview of TNF superfamily: a chest full of potential therapeutic targets Adv. Exp. Med. Biol. 2009, 647, 1-7
2. Sethi, G.; Sung, B.; Kunnumakkara, A. B.; Aggarwal, B. B. Targeting TNF for treatment of cancer and autoimmunity Adv. Exp. Med. Biol. 2009, 647, 37-51
3. Lee, J. C.; Laydon, J. T.; McDonnell, P. C.; Gallagher, T. F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, M. J.; Heys, J. R.; Landvatter, S. W.; Strickler, J. E.; McLaughlin, M. M.; Siemens, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.; Adams, J. L.; Young, P. R. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis Nature 1994, 372, 739-746
4. Pugsley, M. K. Etanercept. Immunex Curr. Opin. Invest. Drugs 2001, 2, 1725-1731
5. Bondeson, J.; Maini, R. N. Tumour necrosis factor as a therapeutic target in rheumatoid arthritis and other chronic inflammatory diseases: the clinical experience with infliximab (Remicade) Int. J. Clin. Pract 2001, 55, 211-216
6. Saleem, B.; Mackie, S.; Emery, P. Infliximab for rheumatoid arthritis Expert Rev. Clin. Immunol. 2006, 2, 193-207 (Pubitemid 44355580)
7. Cottone, M.; Mocciaro, F.; Modesto, I. Infliximab and ulcerative colitis Expert Opin. Biol. Ther. 2006, 6, 401-408
8. Miyasaka, N. Adalimumab for the treatment of rheumatoid arthritis Expert Rev. Clin. Immunol. 2009, 5, 19-26
9. Schieven, G. L. The biology of p38 kinase: a central role in inflammation Curr. Top. Med. Chem. 2005, 5, 921-928 (Pubitemid 41582124)
10. Feldmann, M.; Brennan, F. M.; Maini, R. N. Role of cytokines in rheumatoid arthritis Annu. Rev. Immunol. 1996, 14, 397-440 (Pubitemid 26130190)
11. Wagner, G.; Laufer, S. Small molecular anti-cytokine agents Med. Res. Rev. 2006, 26, 1-62 (Pubitemid 43994929)
12. Adams, J. L.; Badger, A. M.; Kumar, S.; Lee, J. C. p38 MAP kinase: molecular target for the inhibition of pro-inflammatory cytokines Prog. Med. Chem. 2001, 38, 1-60
13. Margutti, S.; Laufer, S. A. Are MAP kinases drug targets? Yes, but difficult ones ChemMedChem 2007, 2, 1116-40
14. Goldstein, D. M.; Kuglstatter, A.; Lou, Y.; Soth, M. J. Selective p38α inhibitors clinically evaluated for the treatment of chronic inflammatory disorders J. Med. Chem. 2010, 53, 2345-2353
15. Lee, M. R.; Dominguez, C. MAP kinase p38 inhibitors: clinical results and an intimate look at their interactions with p38 alpha protein Curr. Med. Chem 2005, 12, 2979-2994 (Pubitemid 41672487)
16. Colletti, S. L.; Frie, J. L.; Dixon, E. C.; Singh, S. B.; Choi, B. K.; Scapin, G.; Fitzgerald, C. E.; Kumar, S.; Nichols, E. A.; O'Keefe, S. J.; O'Neill, E. A.; Porter, G.; Samuel, K.; Schmatz, D. M.; Schwartz, C. D.; Shoop, W. L.; Thompson, C. M.; Thompson, J. E.; Wang, R.; Woods, A.; Zaller, D. M.; Doherty, J. B. Hybrid-designed inhibitors of p38 MAP kinase utilizing N -arylpyridazinones J. Med. Chem. 2003, 46, 349-352 (Pubitemid 36139785)
17. Miwatashi, S.; Arikawa, Y.; Kotani, E.; Miyamoto, M.; Naruo, K.; Kimura, H.; Tanaka, T.; Asahi, S.; Ohkawa, S. Novel inhibitor of p38 MAP kinase as an anti-TNF-alpha drug: discovery of N -[4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol- 5-yl]-2-pyridyl]benzamide (TAK-715) as a potent and orally active anti-rheumatoid arthritis agent J. Med. Chem. 2005, 48, 5966-5979 (Pubitemid 41324607)
18. Liu, C.; Lin, J.; Wrobleski, S. T.; Lin, S.; Hynes, J.; Wu, H.; Dyckman, A. J.; Li, T.; Wityak, J.; Gillooly, K. M.; Pitt, S.; Shen, D. R.; Zhang, R. F.; McIntyre, K. W.; Salter-Cid, L.; Shuster, D. J.; Zhang, H.; Marathe, P. H.; Doweyko, A. M.; Sack, J. S.; Kiefer, S. E.; Kish, K. F.; Newitt, J. A.; McKinnon, M.; Dodd, J. H.; Barrish, J. C.; Schieven, G. L.; Leftheris, K. Discovery of 4-(5-(cyclopropylcarbamoyl)-2-methylphenylamino)-5-methyl- N -propylpyrrolo[1,2- f ][1,2,4]triazine-6-carboxamide (BMS-582949), a clinical p38alpha MAP kinase inhibitor for the treatment of inflammatory diseases J. Med. Chem. 2010, 53, 6629-6639
19. Regan, J.; Capolino, A.; Cirillo, P. F.; Gilmore, T.; Graham, A. G.; Hickey, E.; Kroe, R. R.; Madwed, J. R.; Moriak, M.; Nelson, R.; Pargellis, C. A.; Swinamer, A.; Torcellini, C.; Tsang, M.; Moss, N. Structure-activity relationships of the p38 alpha MAP kinase inhibitor 1-(5- tert -butyl-2- p -tolyl-2 H -pyrazol-3-yl)-3-[4-(2-morpholin-4-yl-ethoxy)naphthalen-1-yl]urea (BIRB 796) J. Med. Chem. 2003, 46, 4676-4686
20. Iwano, S.; Asaoka, Y.; Akiyama, H.; Takizawa, S.; Nobumasa, H.; Hashimoto, H.; Miyamoto, Y. A possible mechanism for hepatotoxicity induced by BIRB-796, an orally active p38 mitogen-activated protein kinase inhibitor J. Appl. Toxicol. 2011, 31, 671-677
21. Duffy, J. P.; Harrington, E. M.; Salituro, F. G.; Cochran, J. E.; Green, J.; Gao, H. A.; Bemis, G. W.; Evindar, G.; Galullo, V. P.; Ford, P. J.; Germann, U. A.; Wilson, K. P.; Bellon, S. F.; Chen, G. G.; Taslimi, P.; Jones, P.; Huang, C.; Pazhanisamy, S.; Wang, Y. M.; Murcko, M. A.; Su, M. S. S. The discovery of VX-745: a novel and selective p38 α kinase inhibitor ACS Med. Chem. Lett. 2011, 2, 758-763
22. Adams, J. L.; Boehm, J. C.; Kassis, S.; Gorycki, P. D.; Webb, E. F.; Hall, R.; Sorenson, M.; Lee, J. C.; Ayrton, A.; Griswold, D. E.; Gallagher, T. F. Pyrimidinylimidazole inhibitors of CSBP/p38 kinase demonstrating decreased inhibition of hepatic cytochrome P450 enzymes Bioorg. Med. Chem. Lett. 1998, 8, 3111-3116 (Pubitemid 28551630)
23. Collis, A. J.; Foster, M. L.; Halley, F.; Maslen, C.; McLay, I. M.; Page, K. M.; Redford, E. J.; Souness, J. E.; Wilsher, N. E. RPR203494 a pyrimidine analogue of the p38 inhibitor RPR200765A with an improved in vitro potency Bioorg. Med. Chem. Lett. 2001, 11, 693-696 (Pubitemid 32187957)
24. Ozdemir, C.; Akdis, C. A. Discontinued drugs in 2006: pulmonary-allergy, dermatological, gastrointestinal and arthritis drugs Expert Opin. Invest. Drugs 2007, 16, 1327-1344 (Pubitemid 47491404)
25. Yamazaki, H.; Kasahara, C.; Kubota, H.; Kontani, T.; Asano, T.; Mizuhara, H.; Yokomoto, M.; Misumi, K.; Kinoshita, T. Pyridazine Derivatives Used for the Treatment of Pain. WO2007026950, 2007.
26. Ley, S. V.; Thomas, A. W. Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation Angew. Chem., Int. Ed. 2003, 42, 5400-5449 and references therein (Pubitemid 37466273)
27. Brandt, T. A.; Caron, S.; Damon, D. B.; DiBrino, J.; Ghosh, A.; Griffith, D. A.; Kedia, S.; Ragan, J. A.; Rose, P. R.; Vanderplas, B. C.; Wei, L. L. Development of two synthetic routes to CE-178,253, a CB1 antagonist for the treatment of obesity Tetrahedron 2009, 65, 3292-3304
28. Hirai, S.; Kikuchi, H.; Kim, H. S.; Begum, K.; Wataya, Y.; Tasaka, H.; Miyazawa, Y.; Yamamoto, K.; Oshima, Y. Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite J. Med. Chem. 2003, 46, 4351-4359 (Pubitemid 37153015)
29. Arora, V.; Salunkhe, M. M.; Sinha, N.; Sinha, R. K.; Jain, S. Synthesis and antibacterial activity of some aryloxy/thioaryloxy oxazolidinone derivatives Bioorg. Med. Chem. Lett. 2004, 14, 4647-4650 (Pubitemid 39496786)
30. MacKenzie, A. R.; Marchington, A. P.; Middleton, D. S.; Newman, S. D.; Jones, B. C. Structure-activity relationships of 1-alkyl-5-(3,4-dichlorophenyl)- 5-[2-[(3-substituted)-1-azetidinyl]ethyl]-2-piperidones. 1. Selective antagonists of the neurokinin-2 receptor J. Med. Chem. 2002, 45, 5365-5377 (Pubitemid 35429175)
31. Further pharmacological results, including the results of a large kinase panel, will be reported shortly by Terajima, M.; Inoue, T.; Magari, K.; Yamazaki, H.; Higashi, Y.; Mizuhara, H. Anti-Inflammatory effect and selectivity profile of AS1940477, a novel and potent p38 mitogen-activated protein kinase inhibitor.
32. Hirayama, F.; Koshio, H.; Ishihara, T.; Hachiya, S.; Sugasawa, K.; Koga, Y.; Seki, N.; Shiraki, R.; Shigenaga, T.; Iwatsuki, Y.; Moritani, Y.; Mori, K.; Kadokura, T.; Kawasaki, T.; Matsumoto, Y.; Sakamoto, S.; Tsukamoto, S. Discovery of N -[2-hydroxy-6-(4-methoxybenzamido)phenyl]-4-(4-methyl-1,4-diazepan-1-yl) benzamide (darexaban, YM150) as a potent and orally available factor Xa inhibitor J. Med. Chem. 2011, 54, 8051-8065
33. Liu, L. L.; Yang, J.; Zhao, Z. G.; Shi, P. Y.; Liu, X. L. Solvent-free synthesis of indole-based thiosemicarbazones under microwave irradiation J. Chem. Res. 2010, 1, 57-60